Phenyl pyrazole thioamides

ABSTRACT

The present invention discloses amides and thioamides substituted in the α or β position with substituted pyrazoles which are useful as herbicides.

CROSS REFERENCE TO RELATED APPLICATION

This is a division of application Ser. No. 686,548, filed May 14, 1976; which is a continuation-in-part of Ser. No. 524,231, Nov. 15, 1974 now abandoned.

The present invention relates to phenyl pyrazole thioamides, for which the essential material constituting a disclosure thereof is incorporated by reference here from U.S. patent application Ser. No. 686,548, filed May 14, 1976, now U.S. Pat. No. 4,072,498. 

We claim:
 1. A compound of the formula: ##STR1## where R₁ is hydrogen, alkyl of 1 to 7 carbon atoms, inclusive, haloalkyl of 1 to 7 carbon atoms, inclusive, phenyl, benzyl or cycloalkyl of 3 to 6 carbon atoms, inclusive, with the proviso that when R₁ is benzyl or cycloalkyl m = 0; R₂ and R₅ are the same or different and are hydrogen, halogen, alkyl of 1 to 6 carbon atoms, inclusive, haloalkyl of 1 to 6 carbon atoms, inclusive, or phenyl; R₁ and R₂ together with the attached carbon atom can be cycloalkyl of 3 to 6 carbon atoms, inclusive, when m = 0, R₁ is not hydrogen and when m = 1 at least one of R₂ or R₅ is hydrogen; R₃ is hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive, phenyl or benzyl; R₄ is hydrogen or alkyl of from 1 to 6 carbon atoms, inclusive, and R₃ and R₄ can be joined together to form a heterocyclic ring selected from the group consisting of pyrrolidine, or piperidine; A and B are the same or different and are hydrogen, alkyl of from 1 to 6 carbon atoms, inclusive, phenyl, halogen, cyano, haloalkyl of 1 to 6 carbon atoms, inclusive, alkoxy or alkylthio in which the alkyl group is from 1 to 3 carbon atoms, inclusive, or trifluoromethyl and when adjacent can be joined to form a ring of from 5 to 7 carbon atoms, inclusive; where X is halogen, nitro, cyano, acetyl, dimethylcarbamoyl, alkyl, haloalkyl, alkoxy or carboalkoxy in which the alkyl group is from 1 to 3 carbon atoms, inclusive, phenyl, benzyl, 2-phenylethyl and n is 0, 1, or 2or an acid addition salt thereof.
 2. A compound according to claim 1 which is N,N,α,4-tetramethyl-3-phenylpyrazole-1-thioacetamide.
 3. A compound according to claim 1 which is α-(n-butyl)-N,N,4-trimethyl-3-phenylpyrazole-1-thioacetamide.
 4. A compound according to claim 1 which is 4-chloro-N,N,α-trimethyl-3-phenylpyrazole-1-thioacetamide.
 5. A compound according to claim 1 which is α-ethyl-N,N,4-trimethyl-3-phenylpyrazole-1-thioacetamide.
 6. A compound according to claim 1 which is N,N-dimethyl-α,4-dimethyl-3-phenylpyrazole-1-thioactamide.
 7. A compound according to claim 1 which is N,N,α-trimethyl-3-phenylpyrazole-1-thioacetamide.
 8. A compound according to claim 1 which is N,N,α,α,4-pentamethyl-3-phenylpyrazole-1-thioacetamide.
 9. A compound according to claim 1 which is N,N,α,α-tetramethyl-3-phenylpyrazole-1-thioacetamide.
 10. A compound according to claim 1 which is N,α,α,4-tetramethyl-3-phenylpyrazole-1-thioacetamide.
 11. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,N,α-trimethylpyrazole-1-thioacetamide.
 12. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,N,α,α,4-pentamethylpyrazole-1-thioacetamide.
 13. A compound according to claim 1 which is α,4-dimethyl-3-phenylpyrazole-1-thioacetamide.
 14. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,N-diethyl-α,α,4-trimethylpyrazole-1-thioacetamide.
 15. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,α,α,4-tetramethylpyrazole-1-thioacetamide. 